I just don't see the big deal. Singletary himself said he doesn't care but why was he even asked?
The fact of the matter is that it doesn't matter, really. Sure Singletary is a franchise legend and a 10-time Pro Bowler but frankly he isn't even one of the three best MLBs in team history.
Singletary was a very good player, yes, great even, but he had the easiest job in the NFL for much of his career. He was able to move about and get to the ball carrier very easily thanks to one of the best defensive lines ever; Dan Hampton (Hall of Fame), Richard Dent (Hall of Fame), Steve McMichael (second in team history in sacks and a darn good player in his own right). Plus his linebacker mates of Otis Wilson and Wilbur Marshall weren't exactly scrubs.
Singletary is a great player and worthy of the Hall of Fame, but as far as franchise history is concerned I would put him behind Dick Butkus, Bill George and Brian Urlacher. His bulging eyes did as much for his career as anything he did on the field.
Singletary is not even the player most worthy of having his number retired by the Bears. That distinction belongs to Mike Ditka. His number, on the other hand, has been worn by no fewer than 11 players since he last wore it in 1967.
I believe that 20 years is long enough for Singletary's number to be put in mothballs. That's two decades fans have had to celebrate and honor his career. The Bears are already short on numbers, especially when the expanded training camp rosters are considered. Since last spring, offseason and training camp rosters can be 90 players. The Bears already have 13 numbers retired.
This means that players have to double up on numbers but that can be tough because then coaches have to be very careful about who is going out on the field, especially in special teams situations where players from offense and defense are on the field at the same time. It may only be an issue for a couple of preseason games but it's still an issue.
The Bears need to come up with a solution to their retired number issue by having a Ring of Honor. I understand the Chicago Park District does not support this idea because Soldier Field is dedicated to the men and women who have served the country and also because it is a shared stadium and a ring of honor would make it seem more "Bears only."
However, there are plenty of players who are worthy of having their number and/or career honored by the team in some way; Ditka, Singletary, Dent, McMichael, Hampton, Jay Hilgenberg, Jimbo Covert, Doug Buffone, just to name a few.
So why go out of the way to not issue 50 for twenty years when the same hasn't been done for other Hall of Famers and franchise legend-caliber players?
Plus, this could be the passing of the "unofficial not retired, retired number" mantle on to number 54.